


They Say it Hurts the First Time

by heffermonkey



Category: Teen Wolf (TV)
Genre: Anal Sex, Caring, Community: 1-million-words, First Time, Gentleness, Intimacy, Kissing, M/M, Tenderness
Language: English
Status: Completed
Published: 2016-06-06
Updated: 2016-06-06
Packaged: 2018-07-12 15:53:33
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,365
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7112422
Author URL: https://archiveofourown.org/users/heffermonkey/pseuds/heffermonkey
Summary: <blockquote class="userstuff">
              <p>They've built things up slow and steady to reach this step in their relationship.</p>
            </blockquote>





	They Say it Hurts the First Time

“I know it’s kind of cliché to say,” Derek whispered as he held Stiles in his arms. “But you need to relax and stay relaxed as much as possible.”

“Yeah but it’s gonna hurt right? They say it hurts the first time,” Stiles babbled out.

“There’ll be pain,” Derek corrected him. “But then, past the pain is something deeper, something worth experiencing a little pain for. But you have to trust me and you have to relax.”

“I know, I – I’m overthinking,” Stiles agreed with a nod.

“Yeah, something I’ve just tried to dispel or has the last few hours seducing you failed spectacularly,” Derek huffed out. “We won’t do this until you’re absolutely sure.”

“I’m sure,” Stiles whispered after a pause of silence. “I want this.”

“Stiles,” Derek said softly, trying to assure him if he didn’t want to go any further then they would stop.

“I want this,” Stiles said firmly. “I want you.”

“It’s different to what we’ve done so far, no amount of getting you prepared for this really prepares you,” Derek reminded him. “It’ll feel different, way different.”

“Of course it will,” Stiles said, sliding his arms around him. “It’ll be you, all of you and I want this.”

“I can take the pain away, or I can stop at any-,” Derek began before Stiles silenced him with a kiss.

“I know,” Stiles assured him. “I’m ready – we’re ready for this.”

“It’ll be good, I promise,” Derek whispered to him.

“Yeah,” Stiles nodded but there was a nervous look in his eyes even so.

“Turn over,” Derek said gently. “Get comfortable.”

Stiles pressed a kiss to his lips before he rolled onto his stomach and hugged a pillow to his chest as he widened his knees under his, lifting his ass. He took in a few deep breaths and let them out slowly. Derek took a moment to take in his form before he sat up, snagged the lube from the side dresser and moved around the bed so he could kneel between Stiles’ legs.

“I’ll go slow,” Derek promised. “Prep just like all the other times.”

They’d been building up to this, mainly because it was Stiles’ first time and Derek refused to leap in, instead he’d slowly and carefully led his lover up to this point of their relationship, all at a comfortable pace for Stiles. They’d began with fingers, prepping him, letting him get used to the feel of being filled. Then Derek had taken to rimming him, to get Stiles used to feeling good when someone touched his ass and made use of it. Derek had introduced toys slowly also, different sizes so Stiles grew used to the stretch and ache. Everything had led up to this moment, but those experiences would be nothing like this one.

He carefully and slowly prepped Stiles as he’d done countless times before with his fingers, using enough lube that the slide and slick made their entrance and probing easy and gentle. Stiles, used to the prep, relaxed fairly quickly and Derek smoothed a palm over the small of his back as he did so. Everything a positive reminder that this was about pleasure and the enjoyment of the connection.

“Okay?” Derek asked after ten minutes of prep in which Stiles was fully relaxed and reposed. Derek read all the signs as well as sensed his emotions but he needed to hear it also.

“Uh huh,” Stiles said quietly.

“Me now,” Derek said and felt the thrum of tension shiver through Stiles at the notion. “Sshh it’s okay.”

Derek slicked up his cock, smearing it with plenty of lube as he looked over his lover and the inviting pose before him. As they’d prepared for this, Derek had indulged in imagining what it would be like to finally claim Stiles like this but nothing could prepare him for how it would really feel to connect that way. He was nervous himself, because he needed this to be perfect for Stiles, for the both of them and because he wanted it so badly.

He raised up on his knees, holding his cock until the head pressed against Stiles’ entrance. His other hand trailed gentle circles into Stiles’ hip and he listened and looked for any signs of distress as he began to push forward. It wasn’t until he felt Stiles begin opening up to him that he realised he wasn’t getting any reaction at all from him and he ran a palm flat from Stiles’ hip to the small of his back with a careful touch.

“Breathe,” Derek whispered quietly.

He felt and heard Stiles exhale, eliciting a soft groan also before he sucked in another breath sharply.

“Keep breathing,” Derek reminded him even as he kept pushing slowly in, mentally telling himself to breathe at the same time. No amount of prep or playing around with toys could fully prepare them, the feel was incredible, the tight heat pressing in around his cock head. There was a little resistance, the ring of inner muscles not used to this kind of intrusion, Derek paused, easing back and forth with a gentle rocking motion and after a half a minute something gave way and Stiles groaned again with somewhat surprise at the feel.

“Okay – you okay?” Derek questioned quietly, not wanting to dispel the mood or speak too much in Stiles’ silence. For a guy he could usually never shut up, Stiles could be unusually quiet and brooding when they had sex, although equally he also had a mouth on him that would make a sailor blush when he was in the mood to talk dirty.

“Yeah – I’m – I’m okay,” Stiles panted out before pressing his face into the pillow, evidently not in the mood for words for the time being. Derek accepted this was a whole different experience of sex compared to Stiles’ former experiences and so he didn’t press too much for conversation. He wanted Stiles to remember every second of it, long as it was good for him. It certainly felt good for Derek and he relished the tight feel and rush of pleasure that this connection with his lover gave him.

Past the tight rings of muscle now made the entrance much easier and he slipped forward with relative ease although he took his time, still rocking gently to help Stiles accommodate him and get used to the feel. Stiles fell silent again for a few minutes and Derek was taking his time, only halfway in but it already felt amazing when Stiles muttered into the pillow before grunting and lifting up onto his elbows with a moan.

“Der-ek,” Stiles gasped out with a deep groan. “Oh god- fu –stop.”

“You need me to stop?” Derek asked in sudden alarm.

“Right there,” Stiles nodded. “Stop, don’t move-. Need you to just -.”

Derek kept still, as still as possible considering the squeeze of tight heat around his cock making him want to thrust deeper into it, craving the need for more of that feeling.

“Stiles,” He choked out with a growl, needing to know he was alright. “You hurting?”

Stiles was panting and he pushed up onto his hands, the movement making Derek growl low in his throat again. When Stiles looked back at him over his shoulder Derek felt a twist of fire in his belly, he could see Stiles was anything but hurting.

“No – just need to feel this,” Stiles panted out. “You like this – oh god.”

“It’s gonna feel even better,” Derek promised. “If you let me.”

Stiles gave a small, almost imperceptible nod, “Slow.”

“I know,” Derek assured him gently.

“Touch me,” Stiles said quietly. “I like feeling your hands on me.”

Derek smiled at the sentiment lacing Stiles’ voice, having figured early on Stiles was a tactile lover, always needing to touch, be it shoulders, fingers, holding hands, simple little touches every time they passed one another. He smoothed a palm flat against the small of his back and along his spine gently, feeling Stiles relaxing under the touch, like it calmed and centred him.

Derek stroked back down his spine gently, fingertips barely grazing the skin and as he did so moved again, sinking deeper and hearing Stiles’ gasp, head dropping down as he concentrated on not tensing up.

“Yeah stay with me, relax,” Derek whispered, hand spreading over the plain of his back, following the lines of muscle and bone. “You feel so good.”

Another push and Stiles’ gasped out sharply again, this time he did tense up and Derek swallowed down at the tightness which suddenly bore down on his cock.

“Sssh, s’ok, breathe baby breathe,” Derek soothed with a choked gasp of his own.

“Hurts-,” Stiles hissed with a low grunt.

“Painful or like a low, dull ache,” Derek asked in concern. “Talk to me Stiles, tell me what you feel.”

“Ache, it aches,” Stiles said with a pant. “Feels stretched and – and full.”

“I can take it away,” Derek reminded him, rubbing in a small circle over his back.

“No just – just -,” Stiles replied, keeping still and calming himself with slow, easy breaths. Derek closed his eyes and concentrated, not on being half buried in his partner but what his partner was feeling, Stiles’ wasn’t distressed or in serious pain but it was a new experience and with that came uncertainty and fear. “I want to feel this, but - not sure I can take much more.”

Derek opened his eyes and looked down at where they were connected, pressing his hands into the round globes of his ass.

“There isn’t much more to give,” He said playfully, hoping humour would help dispel his lover's nerves.

He was happy to hear Stiles give a soft snort in reaction, “I know this is gonna feel good eventually but right now-.”

“We can try later,” Derek assured him.

“No – no,” Stiles shook his head. “I – I’m getting used to it- a little more yeah?”

“Oh yeah,” Derek promised. “And then – then I’ll make it real good for you.”

“Yeah do that,” Stiles sighed and sank down onto his elbows again, hugging the pillow. “Keep going and don’t stop-.”

“Stiles,” Derek said gently, hands trailing over his skin again, along his back, down his hips, over the curve of his ass. 

“Don’t stop,” Stiles said again. “Please-.”

Derek could feel he was relaxing again and following the request began inching in once more, he’d been truthful, he was already half buried in Stiles and it was getting easier to enter him. Stiles moaned softly but didn’t tense up and Derek didn’t stop, holding his breath as he looked down to see how his cock disappeared into his lovers body until he gave a breathless groan of his own when he was fully buried in him.

“Oh – oh fuck okay,” Derek whispered out, giving Stiles’ hips a squeeze. “I – I’m in – oh fuck I’m in you –.”

Stiles’ nodded silently and Derek paused for a moment to ensure he wasn’t in distress but all he felt from Stiles was a growing urgency and it wasn’t to pull out. It was the pursuit of pleasure as his body reaped the benefits of this new experience.

“I’m gonna move now,” Derek said gently. “Need me to stop, you tell me.”

Another silent nod and for a moment he wished he could see Stiles’ face, especially this first time but this was the best position for him right now, the most comfortable considering. But not seeing his face and being able to read his emotions felt almost disconnected if it weren’t for the fact he understood and knew him so well and could use his senses to recognise any distress and pain from his lover.

Derek began easing out, the slick of the lube making it easy and Stiles’ body was becoming used to him, un-resistant when he pushed in again. Stiles gasped and moaned, tilting his head up and Derek could hear the pleasure lining his voice as he gave in to the feelings. Derek settled into a slow, gentle rhythm, keeping his thrusts shallow but deep so Stiles’ could grow used to the feel of being filled with his cock. Stiles was panting, short soft breaths with gentle groans of pleasure punctuating the air.

Derek leaned down, reaching under him until he wrapped a fist around Stiles’ cock. He’d been hard when they began but had softened a little and Derek slowly and carefully began jacking him off with the same rhythm as he fucked him. Stiles’ made quiet noises at the back of his throat at the feel and Derek smiled, sensing his partner beginning to enjoy the pleasure of their first real coupling. It took a little time but Stiles’ cock grew hard in his hand again, pre-cum gathering at the head and Derek blindly smoothed his thumb through it, creating a little more slick for his fingers to glide over the shaft.

“God you feel good,” Derek groaned, leaning down, his other hand sliding under Stiles and along his torso to his chest, palm flat against his heart so he could physically feel as well as sense the quick palpitations. He pressed his face down, nuzzling along Stiles’ spine and feeling him shudder and arch. “Smell good-.”

Pressing a kiss to the middle of his back he glanced up, Stiles had turned his face, head pressed against the pillow as he breathed and moaned, eyes tight shut, fingers knuckle tight with their grip in the sheets.

“Stiles – you still with me?” Derek asked with a moment of concern.

“Uh – huh,” Stiles choked out. “Don’t – don’t stop. More.”

“I don’t want to hurt you,” Derek reminded him, lips grazing against his skin again.

“Please,” Stiles hissed out. “Move damn it.”

“Great – I got a pushy bottom as a boyfriend,” Derek huffed out teasingly.

“Derek – oh – oh god fuck – oh,” Stiles moaned, words turning to meaningless sounds.

Derek picked up the pace a touch, not as much as he wanted, he held back on pounding him even though the temptation was there but not this time. Not yet, when Stiles was used to being taken like this, then he’d let his guard down a little more. But Stiles was loose now, stretched and open. Derek lifted up, hands back on his hips, gripping tight as he slid in and out, longer strokes this time, letting Stiles feel how he pulled out to the tip before sinking back deep into him again.

“Yeah fuck me – fuh-,” Stiles groaned with a pant. “Yes, Derek.”

Derek could hear it in his voice, used to hearing that particular pitch now after the weeks of exploring his lover's body, what turned him on, what pushed him over the edge.

“Your close,” Derek said through gritted teeth.

“Uh huh,” Stiles panted and gasped in pleasure.

“You wanna come like this Stiles?” Derek growled possessively. “While I fuck you?”

Stiles groaned again, deep and low, Derek knew the signs, the pleasure was building fast now, he was right on that edge but he needed a little more to get him over.

“Touch yourself,” Derek encouraged. “Get yourself off while I fuck you.”

It seemed to take all of Stiles’ strength to move, reaching a hand down under his body and he moaned, a high pitched whine. Derek knew he’d gotten a good grip on himself and watched his shoulder muscles clenching and unclenching as he began to jerk himself off.

“Yeah, good baby,” Derek whispered.

“More,” Stiles panted out. “Please- just a little-.”

Derek closed his eyes tight, the need in Stiles’ voice was like the call of the wolf, sinking into his bones and it was all he could focus on. He tightened his grip, concentrated and felt his veins pulsing as he quickened his pace again, deep, hammering movements as he fucked hard and fast into the tight grip of his lovers hole. He took away the pain at that moment, giving his lover what he needed but refusing to let him feel too much pain for it. He didn’t ever want Stiles to be afraid of what he asked for or associate any part of their love making with pain.

“Derek – yes, yes fuck, Derek!” Stiles yelled out and he could feel it, the scent of his pleasure a heady, musky scent that Derek knew well. 

Derek choked and gasped as Stiles came, his ass tightening around his cock as his hips stuttered, cock pulsing as his balls emptied. Derek stilled and rubbed a circle into his back as he came over and over, moaning and panting from the exertion until Stiles lay still and quiet, quivering from the orgasm that had rocked through his body. Derek sucked in a breath, easing out of him as Stiles gave a soft whine of sensitivity. As much as Derek wanted to keep pounding him until his own oblivion, Stiles wasn’t ready for that yet. Instead Derek took himself in hand, looking over his lovers spent body with affection and lust as he jerked his cock quickly in his fist, a hand on Stiles’ hip. It was as Stiles looked back at him over his shoulder, locking eyes with him and giving one of those trademark smiles that Derek loved so much that he came hard, Stiles’ name on his lips, thick white creamy streaks of come painting over his back and ass. When he was done, Derek dropped to the side of him, suddenly devoid of strength, an arm wrapped around Stiles who was unmoving and breathing hard.

“Fuck that was-,” Stiles began, searching for a word and finding nothing was apt to describe the moment.

“Yeah, it was,” Derek agreed. He was never a man of many words so he was happy and content with the implication.

They lay quiet and still as they got their breath back, Stiles easing out of his position and stretching out beside him instead, and arm around his waist, a leg resting over his as he buried his face in the crook of his neck.

“You okay?” Derek asked with a small frown, senses picking up on some kind of distress on Stiles’ part. 

“It was amazing, but it aches now,” Stiles replied honestly.

“Want me to -,” Derek began to ask.

“No – no I think I need to experience this,” Stiles told him. “It doesn’t hurt, it’s a little uncomfortable but - it’s a good kind of ache.”

“Let’s take a shower and I can check I didn’t damage you,” Derek smiled, sitting up and tugging at his arm.

“You didn’t,” Stiles shook his head as he was pulled from the bed onto shaky, wobbly legs.

“I’d like to check anyway,” Derek said, sliding an arm around him.

“Any excuse to ogle my ass huh?” Stiles said playfully but he appreciated the aftercare.

“I don’t need an excuse to do that,” Derek huffed out a laugh as Stiles leaned on him and they made it into the bathroom, all limbs and stolen kisses. Stiles was always particularly touchy feely after they’d had sex so it didn’t surprise him that he was acting particularly clingy right then. Derek turned on the shower and held him close as he waited for the warm water to come through. “You really okay?”

“Oh yeah,” Stiles grinned. “Was different to what I expected, in a good way. Way better than any toy.”

“A few more days and we can try it again,” Derek smiled.

“Why wait?” Stiles frowned with a pout.

“Believe me you’re riding the high right now but in a few hours you may not feel the same way, you’ll want your body to adjust,” Derek assured him. “Anyway there isn’t any rush. Waiting only builds the anticipation and there’ll be nothing more I want to do than be connected with you like that again. When you’re ready.”

Stiles took his explanation in with a sombre expression, smiling softly and reeling him in for a gentle kiss.

“You’re no sourwolf,” Stiles laughed gently against his mouth. “More like a love sick cub.”

“Get in the shower,” Derek rolled his eyes, giving his ass a pinch as he moved them under the spray, trying to hide his grin.

~ fin ~


End file.
